Sodium ethanethiolate → HCID 9847371, compound

HRID 2211382Notes

Reaction equation

HRID 2211382 reaction equation
[CH2:1]([C:5]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:26]([O:36]C)=[CH:25][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[CH2:2][CH2:3][CH3:4].C([S-])C.[Na+]>CN(C)C=O.Cl>[CH2:1]([C:5]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:26]([OH:36])=[CH:25][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 19375840HCID 19375840, compound

Product 1

HCID 9847371HCID 9847371, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 3-(2-(3-(2-butyl-4-(4-fluorophenyl)-5-methoxyphenoxy)propoxy)phenyl)propionate and 5 equivalents of sodium ethanthiolate in dimethylformamide was heated at 110° C. for 2 hours, cooled, diluted with aqueous hydrochloric acid, and extracted with ethyl acetate. The organic solution was washed with water, dried, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl ether and with ethyl acetate providing the desired title product in 66% yield. NMR.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with water
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl ether and with ethyl acetate providing the desired title product in 66% yield

Sources & evidence

ORD record
ord-ae94447856c44895bc3da9db17bac711
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

Loading…